CA2475011C - Method for analysis of compounds with amino group and analytical reagent therefor - Google Patents
Method for analysis of compounds with amino group and analytical reagent therefor Download PDFInfo
- Publication number
- CA2475011C CA2475011C CA2475011A CA2475011A CA2475011C CA 2475011 C CA2475011 C CA 2475011C CA 2475011 A CA2475011 A CA 2475011A CA 2475011 A CA2475011 A CA 2475011A CA 2475011 C CA2475011 C CA 2475011C
- Authority
- CA
- Canada
- Prior art keywords
- group
- compound
- carbamate
- reagent
- amino group
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Expired - Lifetime
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- 125000003277 amino group Chemical group 0.000 title claims abstract description 99
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- 238000004949 mass spectrometry Methods 0.000 claims abstract description 29
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- 229910052757 nitrogen Inorganic materials 0.000 claims description 23
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- FEMOMIGRRWSMCU-UHFFFAOYSA-N ninhydrin Chemical compound C1=CC=C2C(=O)C(O)(O)C(=O)C2=C1 FEMOMIGRRWSMCU-UHFFFAOYSA-N 0.000 description 1
- 229910017604 nitric acid Inorganic materials 0.000 description 1
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- 239000002245 particle Substances 0.000 description 1
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Classifications
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- G01N33/48—Biological material, e.g. blood, urine; Haemocytometers
- G01N33/50—Chemical analysis of biological material, e.g. blood, urine; Testing involving biospecific ligand binding methods; Immunological testing
- G01N33/58—Chemical analysis of biological material, e.g. blood, urine; Testing involving biospecific ligand binding methods; Immunological testing involving labelled substances
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D207/00—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom
- C07D207/46—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with hetero atoms directly attached to the ring nitrogen atom
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- G—PHYSICS
- G01—MEASURING; TESTING
- G01N—INVESTIGATING OR ANALYSING MATERIALS BY DETERMINING THEIR CHEMICAL OR PHYSICAL PROPERTIES
- G01N33/00—Investigating or analysing materials by specific methods not covered by groups G01N1/00 - G01N31/00
- G01N33/48—Biological material, e.g. blood, urine; Haemocytometers
- G01N33/50—Chemical analysis of biological material, e.g. blood, urine; Testing involving biospecific ligand binding methods; Immunological testing
- G01N33/68—Chemical analysis of biological material, e.g. blood, urine; Testing involving biospecific ligand binding methods; Immunological testing involving proteins, peptides or amino acids
- G01N33/6803—General methods of protein analysis not limited to specific proteins or families of proteins
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- G—PHYSICS
- G01—MEASURING; TESTING
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- G01N33/48—Biological material, e.g. blood, urine; Haemocytometers
- G01N33/50—Chemical analysis of biological material, e.g. blood, urine; Testing involving biospecific ligand binding methods; Immunological testing
- G01N33/68—Chemical analysis of biological material, e.g. blood, urine; Testing involving biospecific ligand binding methods; Immunological testing involving proteins, peptides or amino acids
- G01N33/6803—General methods of protein analysis not limited to specific proteins or families of proteins
- G01N33/6806—Determination of free amino acids
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- G—PHYSICS
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- G01N33/48—Biological material, e.g. blood, urine; Haemocytometers
- G01N33/50—Chemical analysis of biological material, e.g. blood, urine; Testing involving biospecific ligand binding methods; Immunological testing
- G01N33/68—Chemical analysis of biological material, e.g. blood, urine; Testing involving biospecific ligand binding methods; Immunological testing involving proteins, peptides or amino acids
- G01N33/6803—General methods of protein analysis not limited to specific proteins or families of proteins
- G01N33/6848—Methods of protein analysis involving mass spectrometry
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- G—PHYSICS
- G01—MEASURING; TESTING
- G01N—INVESTIGATING OR ANALYSING MATERIALS BY DETERMINING THEIR CHEMICAL OR PHYSICAL PROPERTIES
- G01N2458/00—Labels used in chemical analysis of biological material
- G01N2458/15—Non-radioactive isotope labels, e.g. for detection by mass spectrometry
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- G—PHYSICS
- G01—MEASURING; TESTING
- G01N—INVESTIGATING OR ANALYSING MATERIALS BY DETERMINING THEIR CHEMICAL OR PHYSICAL PROPERTIES
- G01N2560/00—Chemical aspects of mass spectrometric analysis of biological material
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- Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
- Y10—TECHNICAL SUBJECTS COVERED BY FORMER USPC
- Y10T—TECHNICAL SUBJECTS COVERED BY FORMER US CLASSIFICATION
- Y10T436/00—Chemistry: analytical and immunological testing
- Y10T436/13—Tracers or tags
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- Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
- Y10—TECHNICAL SUBJECTS COVERED BY FORMER USPC
- Y10T—TECHNICAL SUBJECTS COVERED BY FORMER US CLASSIFICATION
- Y10T436/00—Chemistry: analytical and immunological testing
- Y10T436/14—Heterocyclic carbon compound [i.e., O, S, N, Se, Te, as only ring hetero atom]
-
- Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
- Y10—TECHNICAL SUBJECTS COVERED BY FORMER USPC
- Y10T—TECHNICAL SUBJECTS COVERED BY FORMER US CLASSIFICATION
- Y10T436/00—Chemistry: analytical and immunological testing
- Y10T436/14—Heterocyclic carbon compound [i.e., O, S, N, Se, Te, as only ring hetero atom]
- Y10T436/145555—Hetero-N
-
- Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
- Y10—TECHNICAL SUBJECTS COVERED BY FORMER USPC
- Y10T—TECHNICAL SUBJECTS COVERED BY FORMER US CLASSIFICATION
- Y10T436/00—Chemistry: analytical and immunological testing
- Y10T436/24—Nuclear magnetic resonance, electron spin resonance or other spin effects or mass spectrometry
Landscapes
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- Health & Medical Sciences (AREA)
- Engineering & Computer Science (AREA)
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- Urology & Nephrology (AREA)
- Immunology (AREA)
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- Pathology (AREA)
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- General Health & Medical Sciences (AREA)
- Biophysics (AREA)
- Proteomics, Peptides & Aminoacids (AREA)
- Spectroscopy & Molecular Physics (AREA)
- Other Investigation Or Analysis Of Materials By Electrical Means (AREA)
- Plural Heterocyclic Compounds (AREA)
- Pyrrole Compounds (AREA)
- Investigating Or Analysing Biological Materials (AREA)
Applications Claiming Priority (3)
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| JP2002036446 | 2002-02-14 | ||
| JP2002-36446 | 2002-02-14 | ||
| PCT/JP2003/001463 WO2003069328A1 (en) | 2002-02-14 | 2003-02-13 | Method of analyzing aminofunctional compound and analytical reagent |
Publications (2)
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| CA2475011A1 CA2475011A1 (en) | 2003-08-21 |
| CA2475011C true CA2475011C (en) | 2015-07-07 |
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| EP (3) | EP2317307B1 (enExample) |
| JP (6) | JP4453363B2 (enExample) |
| AU (1) | AU2003211941A1 (enExample) |
| CA (1) | CA2475011C (enExample) |
| WO (1) | WO2003069328A1 (enExample) |
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| EP2317307B1 (en) * | 2002-02-14 | 2013-11-20 | Ajinomoto Co., Inc. | Method of analyzing amino- and/or imino-functional compounds, and analytical reagent |
| US20050014279A1 (en) * | 2003-07-14 | 2005-01-20 | Nguyen Hoa Duc | Method of analysis of amine by mass spectrometry |
| JP4714584B2 (ja) * | 2003-11-21 | 2011-06-29 | エーザイ・アール・アンド・ディー・マネジメント株式会社 | 同位体標識化内部標準物質を用いる定量方法、該定量方法を実行する解析システムおよび該解析のためのプログラム |
| US20080206737A1 (en) * | 2004-05-19 | 2008-08-28 | Hunter Christie L | Expression quantification using mass spectrometry |
| US20070054345A1 (en) * | 2004-05-19 | 2007-03-08 | Hunter Christie L | Expression quantification using mass spectrometry |
| WO2005116629A1 (ja) * | 2004-05-26 | 2005-12-08 | Ajinomoto Co., Inc. | アミノ官能性化合物の分析方法及び装置 |
| WO2006017208A1 (en) * | 2004-07-12 | 2006-02-16 | Applera Corporation | Mass tags for quantitative analyses |
| US20070048752A1 (en) | 2004-07-12 | 2007-03-01 | Applera Corporation | Mass tags for quantitative analyses |
| US8969089B2 (en) | 2004-10-12 | 2015-03-03 | Quest Diagnostics Investments, Inc. | Analysis of amino acids in body fluid by liquid chromatography-mass spectrometry |
| US20060183238A1 (en) | 2005-02-09 | 2006-08-17 | Applera Corporation | Amine-containing compound analysis methods |
| JP2007163423A (ja) * | 2005-12-16 | 2007-06-28 | Ajinomoto Co Inc | 質量分析計によるアミノ酸分析方法 |
| CN101379074A (zh) * | 2006-02-08 | 2009-03-04 | 日本电气株式会社 | 修饰肽的方法和鉴定肽的方法 |
| EP1983346A4 (en) * | 2006-02-08 | 2010-03-17 | Nec Corp | METHOD FOR CLEAVING A PEPTIDE BOND AT THE C-TERMINAL END OF A PEPTIDE, AND A METHOD FOR DETERMINING THE C-TERMINAL END-ACE AMINO ACID SEQUENCE OF A PEPTIDE |
| US12367163B2 (en) | 2007-06-29 | 2025-07-22 | Quest Diagnostics Investments Llc | Analysis of amino acids in body fluid by liquid chromatography—mass spectrometry |
| JP5517931B2 (ja) * | 2007-06-29 | 2014-06-11 | クエスト ダイアグノスティックス インヴェストメンツ インコーポレイテッド | 液体クロマトグラフィー質量分析による体液中のアミノ酸分析 |
| EP2209001A4 (en) | 2007-10-25 | 2010-10-27 | Ajinomoto Kk | METHOD FOR ASSESSING STROKEN GLUCOSE TOLERANCE |
| EP2215460A4 (en) * | 2007-11-26 | 2010-12-29 | Waters Technologies Corp | INTERNAL STANDARDS AND METHODS FOR USE IN MEASURING QUANTITATIVELY ANALYTES IN A SAMPLE |
| ES2608484T3 (es) * | 2008-02-04 | 2017-04-11 | Prozyme, Inc. | Compuestos y métodos para un marcaje rápido de N-glicanos |
| DE102009060102A1 (de) * | 2009-12-21 | 2011-06-22 | Martin-Luther-Universität Halle-Wittenberg, 06108 | Derivatisierungsreagenzien zur tandem-massenspektrometrischen Quantifizierung von Proteinen |
| KR102002770B1 (ko) | 2011-07-21 | 2019-07-24 | 후지필름 와코 준야꾸 가부시키가이샤 | 혈장중 아미노산 분석용 표준액 |
| WO2013049622A1 (en) | 2011-09-28 | 2013-04-04 | Waters Technologies Corporation | Rapid fluorescence tagging of glycans and other biomolecules with enhanced ms signals |
| US10436790B2 (en) | 2011-09-28 | 2019-10-08 | Waters Technologies Corporation | Rapid fluorescence tagging of glycans and other biomolecules with enhanced MS signals |
| US11352325B2 (en) | 2011-09-28 | 2022-06-07 | Waters Technologies Corporation | Rapid fluorescence tagging of glycans and other biomolecules with enhanced MS signals |
| JP6444736B2 (ja) | 2011-11-23 | 2018-12-26 | クエスト ダイアグノスティックス インヴェストメンツ インコーポレイテッド | タンデム質量分析によるキスペプチン−５４の検出 |
| JP6269502B2 (ja) | 2012-11-27 | 2018-01-31 | 味の素株式会社 | 膵臓癌の評価方法、膵臓癌評価装置、膵臓癌評価方法、膵臓癌評価プログラム、膵臓癌評価システムおよび端末装置 |
| JP7055634B2 (ja) | 2014-10-30 | 2022-04-18 | ウオーターズ・テクノロジーズ・コーポレイシヨン | 標識化グリコシルアミンの迅速調製およびそれを生成するグリコシル化生体分子の分析方法 |
| EP3744708B1 (en) | 2014-11-13 | 2023-08-09 | Waters Technologies Corporation | Calibrant for liquid chromatography calibration of labeled n-glycans |
| KR101627841B1 (ko) * | 2015-05-27 | 2016-06-07 | 다이아텍코리아 주식회사 | 싸이오크로멘 타입 화합물 및 그 용도 |
| EP3304051B1 (en) | 2015-05-29 | 2020-08-26 | Agilent Technologies, Inc. | Compounds for labeling amine-containing compounds, and their use |
| CN105548432A (zh) * | 2015-12-18 | 2016-05-04 | 乐普药业股份有限公司 | 一种比伐卢定中氨基酸的检测分析方法 |
| CN117054585A (zh) | 2016-04-24 | 2023-11-14 | 沃特世科技公司 | 用于对用两亲强碱性部分改性的聚糖进行分析的带电表面反相色谱材料方法 |
| EP4234062A3 (en) | 2016-06-21 | 2023-10-25 | Waters Technologies Corporation | Methods of electrospray ionization of glycans modified with amphipathic, strongly basic moieties |
| EP3472132A4 (en) | 2016-06-21 | 2020-01-15 | Waters Technologies Corporation | FLUORESCENCE LABELING OF GLYCANS AND OTHER BIOMOLECULES BY REDUCING AMINATION FOR IMPROVED MASS SPECTROMETRY SIGNALS |
| PT3480599T (pt) | 2016-06-30 | 2024-10-18 | Ajinomoto Kk | Método de avaliação da cetose pós-parto |
| WO2018005139A1 (en) | 2016-07-01 | 2018-01-04 | Waters Technologies Corporation | Methods for the rapid preparation of labeled glycosylamines from complex matrices using molecular weight cut off filtration and on-filter deglycosylation |
| CN110023763A (zh) | 2016-10-03 | 2019-07-16 | 沃特世科技公司 | 可用于lc-ms分析的标记的聚糖氨基酸复合物及其制备方法 |
| KR20200052329A (ko) * | 2017-09-08 | 2020-05-14 | 에프. 호프만-라 로슈 아게 | 질량 분석법용의 설폭사이드 기반 시약 |
| JP7151723B2 (ja) | 2017-12-28 | 2022-10-12 | 味の素株式会社 | 給餌管理システムおよび給餌管理方法 |
| WO2020067386A1 (ja) | 2018-09-26 | 2020-04-02 | 味の素株式会社 | 軽度認知障害の評価方法、算出方法、評価装置、算出装置、評価プログラム、算出プログラム、記録媒体、評価システムおよび端末装置 |
| CN113624862B (zh) * | 2021-07-13 | 2023-04-07 | 清华大学 | 一种覆盖多种代谢物的代谢组和代谢流分析方法和试剂盒 |
| CN114354801B (zh) * | 2021-12-31 | 2023-07-18 | 山东大学 | （R）-3-Boc-氨基哌啶中三种氨基吡啶异构体含量的分析方法 |
| CN115925614B (zh) * | 2022-12-02 | 2024-03-08 | 中山大学 | 用于发现可与醛基反应的活性物质的小分子探针 |
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| US4003912A (en) * | 1973-06-11 | 1977-01-18 | Monsanto Company | Dicarboximido-N-phenylsubstituted carbamates and derivatives |
| JPS5855754A (ja) | 1981-09-30 | 1983-04-02 | Hitachi Ltd | アミノ酸分析方法 |
| JPS6444848A (en) | 1987-08-14 | 1989-02-17 | Hitachi Ltd | Analysis of amino acid |
| US5296599A (en) | 1991-09-19 | 1994-03-22 | Millipore Corporation | Activated carbamates compounds |
| AU687109B2 (en) * | 1994-07-08 | 1998-02-19 | City Of Hope | N-terminal protein sequencing reagents and methods which form amino acid derivatives |
| JP3346965B2 (ja) | 1995-09-14 | 2002-11-18 | 株式会社日立製作所 | アミノ酸分析装置 |
| TW358097B (en) * | 1996-05-24 | 1999-05-11 | Hoffmann La Roche | Beta-lactams and their process and pharmaceutical compositions |
| JP4085443B2 (ja) | 1997-05-07 | 2008-05-14 | 株式会社島津製作所 | アミノ酸の分析試薬及びアミノ酸の分析方法 |
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| GB9821393D0 (en) | 1998-10-01 | 1998-11-25 | Brax Genomics Ltd | Protein profiling 2 |
| US6629040B1 (en) * | 1999-03-19 | 2003-09-30 | University Of Washington | Isotope distribution encoded tags for protein identification |
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| JP4505905B2 (ja) | 1999-11-22 | 2010-07-21 | 住友化学株式会社 | ペプチドのアミノ酸配列決定方法 |
| JP3341041B2 (ja) * | 2000-02-23 | 2002-11-05 | 独立行政法人産業技術総合研究所 | ペプチドのアミノ酸配列解析方法 |
| AUPQ664300A0 (en) * | 2000-04-03 | 2000-05-04 | Proteome Systems Ltd | Macromolecule detection |
| US6716634B1 (en) * | 2000-05-31 | 2004-04-06 | Agilent Technologies, Inc. | Increasing ionization efficiency in mass spectrometry |
| WO2002004936A1 (fr) * | 2000-07-11 | 2002-01-17 | Japan Science And Technology Corporation | Sonde pour spectrometrie de masse d'un echantillon liquide |
| US20060141632A1 (en) | 2000-07-25 | 2006-06-29 | The Procter & Gamble Co. | New methods and kits for sequencing polypeptides |
| JP3508710B2 (ja) | 2000-09-01 | 2004-03-22 | 株式会社日立製作所 | アミノ酸分析方法および装置 |
| ATE320007T1 (de) * | 2000-10-23 | 2006-03-15 | Inst Genetics Llc | Säureempfindliches isotop-codiertes extrahiermittel (alice) in massenspectrometrieanalyse |
| AU2002241732B2 (en) * | 2000-10-23 | 2007-07-12 | Genetics Institute, Llc | Isotope-coded ionization-enhancing reagents (ICIER) for high-throughput protein identification and quantitation using matrix-assisted laser desorption ionization mass spectrometry |
| US20030045552A1 (en) * | 2000-12-27 | 2003-03-06 | Robarge Michael J. | Isoindole-imide compounds, compositions, and uses thereof |
| US6818454B2 (en) * | 2001-02-16 | 2004-11-16 | Battelle Memorial Institute | Phosphoprotein binding agents and methods of their use |
| JP3464665B2 (ja) | 2002-01-07 | 2003-11-10 | 株式会社日立製作所 | アミノ酸分析装置 |
| EP2317307B1 (en) | 2002-02-14 | 2013-11-20 | Ajinomoto Co., Inc. | Method of analyzing amino- and/or imino-functional compounds, and analytical reagent |
| WO2005116629A1 (ja) * | 2004-05-26 | 2005-12-08 | Ajinomoto Co., Inc. | アミノ官能性化合物の分析方法及び装置 |
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| JP5136542B2 (ja) | 2013-02-06 |
| EP1475632A1 (en) | 2004-11-10 |
| JP2018052972A (ja) | 2018-04-05 |
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| JP6699645B2 (ja) | 2020-05-27 |
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| EP2317307A3 (en) | 2012-03-14 |
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| EP2317307B1 (en) | 2013-11-20 |
| JP6278210B2 (ja) | 2018-02-14 |
| JP2010071995A (ja) | 2010-04-02 |
| EP2336763A1 (en) | 2011-06-22 |
| AU2003211941A1 (en) | 2003-09-04 |
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